Water → 1-(2-Methylpyrimidin-5-yl)-4-oxocyclohexanecarbonitrile

HRID 512181Notes

Reaction equation

HRID 512181 reaction equation
[C:1]([C:3]1([C:14]2[CH:15]=[N:16][C:17]([CH3:20])=[N:18][CH:19]=2)[CH2:8][C:7](C(OC)=O)=[C:6]([OH:13])[CH2:5][CH2:4]1)#[N:2].[Na+].[Cl-].O>CS(C)=O>[CH3:20][C:17]1[N:16]=[CH:15][C:14]([C:3]2([C:1]#[N:2])[CH2:4][CH2:5][C:6](=[O:13])[CH2:7][CH2:8]2)=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 5234Sodium ChlorideHCID 86716207Methyl 5-cyano-2-hydroxy-5-(2-methylpyrimidin-5-yl)cyclohex-1-enecarboxylate

Product 1

HCID 867162081-(2-Methylpyrimidin-5-yl)-4-oxocyclohexanecarbonitrileYield 41%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of methyl 5-cyano-2-hydroxy-5-(2-methylpyrimidin-5-yl)cyclohex-1-enecarboxylate (6.2 g, 0.023 mol), NaCl (1.46 g, 0.025 mol) and H2O (1.24 mL, 0.069 mol) in DMSO (50 mL) was heated to 160° C. for 3 h. After cooling to room temperature, the reaction was added water and extracted with EtOAc (6×100 mL). The organic layer was washed with brine, dried over Na2SO4 and concentracted. The crude product was purified by flash chromatography(EtOAc: Petroluem ether=1:3˜3:2) to give 1-(2-methylpyrimidin-5-yl)-4-oxocyclohexanecarbonitrile (2 g, yield: 41%). 1H NMR (CDCl3 400 MHz): δ8.80 (s, 2H), 3.00-2.90 (m, 2H), 2.77 (s, 3H), 2.70-2.60 (m, 2H), 2.60-2.50 (m, 2H), 2.40-2.25 (m, 1H).

Workup

  1. extractionextracted with EtOAc (6×100 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe crude product was purified by flash chromatography(EtOAc: Petroluem ether=1:3˜3:2)

Sources & evidence

ORD record
ord-616758bcfd6640deafe0c73b4c4a4491
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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